Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (–)-Levoglucosenone

2017 ◽  
Vol 70 (10) ◽  
pp. 1146 ◽  
Author(s):  
Edward T. Ledingham ◽  
Kieran P. Stockton ◽  
Ben W. Greatrex
Keyword(s):  
Protease Inhibitor ◽  
Acid Catalysis ◽  
Traditional Approach ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
Biomass Pyrolysis ◽  
Strong Base ◽  
Bicyclic System ◽  
Chiral Synthon

Lignocellulosic biomass pyrolysis with acid catalysis selectively produces the useful chiral synthon 6,8-dioxabicyclo[3.2.1]oct-2-ene-4-one ((–)-levoglucosenone, LGO). In this report, LGO was used to prepare (3R,5S)-3-benzyl-5-(hydroxymethyl)-4,5-dihydrofuran-2(3H)-one, which is an intermediate used in the construction of antivirals including the protease inhibitor indinavir. To achieve the synthesis, the hydrogenated derivative of LGO was functionalised using aldol chemistry and various aromatic aldehydes were used to show the scope of the reaction. Choice of base affected reaction times and the best yields were obtained using 1,1,3,3-tetramethylguanidine. Hydrogenation of the α-benzylidene-substituted bicyclic system afforded a 4 : 3 equatorial/axial mixture of isomers, which was equilibrated to a 97 : 3 mixture under basic conditions. Subsequent Baeyer–Villiger reaction afforded the target lactone in 57 % overall yield for four steps, a route that avoids the protection and strong base required in the traditional approach. The aldol route is contrasted with the α-alkylation and a Baylis–Hillman approach that also both start with LGO.

Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate

2017 ◽  
Vol 41 (3) ◽  
pp. 136-138 ◽  
Author(s):  
Sabereh Bougan ◽  
Alireza Hassanabadi
Keyword(s):  
Green Chemistry ◽  
Organic Solvent ◽  
Green Synthesis ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

scholarly journals One-pot Three-component Synthesis of β-amino Carbonyl Compounds Using Nanocrystalline Solid Acid Catalyst

2013 ◽  
Vol 1 ◽  
pp. 194308921350716 ◽  
Author(s):  
Abbas Teimouri ◽  
Leila Ghorbanian
Keyword(s):  
Carbonyl Compounds ◽  
Organic Molecules ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
One Pot ◽  
The Mannich Reaction

This study presents a simple highly versatile and efficient synthesis of various β-amino carbonyl compounds in the Mannich reaction of acetophenone with aromatic aldehydes and aromatic amines in the presence of nanosulfated zirconia, nanostructured ZnO, nano-γ-alumina, and nano-ZSM-5 zeolites as the catalyst in ethanol at moderate temperature. The optical properties of the nanostructured organic molecules were studied. The advantages of methods are short reaction times, milder conditions, easy workup, and purification of products by nonchromatographic methods. The catalysts can be recovered for the subsequent reactions and reused without any appreciable loss of efficiency.

Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media

2014 ◽  
Vol 68 (8) ◽  
Author(s):  
Hamzeh Kiyani ◽  
Fatemeh Ghorbani
Keyword(s):  
Organic Solvent ◽  
Aqueous Media ◽  
Ethyl Cyanoacetate ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields

Abstract2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.

Synthesis of hexahydro-4-phenylquinoline-3-carbonitriles using Fe3O4@SiO2-SO3H nanoparticles as a superior and retrievable heterogeneous catalyst under ultrasonic irradiations

2018 ◽  
Vol 73 (5) ◽  
pp. 269-274 ◽  
Author(s):  
Javad Safaei-Ghomi ◽  
Reza Aghagoli ◽  
Hossein Shahbazi-Alavi
Keyword(s):  
Heterogeneous Catalyst ◽  
Alternative Energy ◽  
Ammonium Acetate ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Green Process ◽  
Alternative Energy Source

AbstractAn efficient synthesis of hexahydro-4-phenylquinoline-3-carbonitriles is described by the four-component condensation reaction of cyclohexanone, ammonium acetate, malononitrile, and aromatic aldehydes using Fe3O4@SiO2-SO3H nanoparticles as a superior and retrievable heterogeneous catalyst under ultrasonic irradiations. The reusability of the catalyst and little catalyst loading, excellent yields, short reaction times, using the sonochemical procedure as a green process and an alternative energy source are some benefits of this method.

scholarly journals Efficient Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones using Ionic Liquid Pyrazinium Di(hydrogen sulfate) {Py(HSO4)2} as a Novel, Green and Homogeneous Catalyst

2017 ◽  
Vol 56 (4) ◽  
Author(s):  
Abdolkarim Zare ◽  
Roghayyeh Khanivar ◽  
Marzieh Hatami ◽  
Mohammad Mokhlesi ◽  
Mohammad Ali Zolfigol ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Homogeneous Catalyst ◽  
Hydrogen Sulfate ◽  
Efficient Synthesis ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
The One ◽  
High Yields

An efficient and simple solvent-free procedure for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[<em>a</em>]-xanthen-11-one derivatives <em>via</em> the one-pot multi-component condensation of dimedone with aromatic aldehydes and β-naphthol in the presence of protic acidic ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO<sub>4</sub>)<sub>2</sub>} as a green and homogeneous catalyst is described. All reactions proceed efficiently, and the title compounds are produced in high yields and in short reaction times.

Chlorosulfonic Acid Supported Piperidine-4-carboxylic Acid (PPCA) Functionalized Fe3O4 Nanoparticles (Fe3O4-PPCA): The Efficient, Green and Reusable Nanocatalyst for the Synthesis of Pyrazolyl Coumarin Derivatives under Solvent-Free Conditions

2019 ◽  
Vol 22 (2) ◽  
pp. 123-128
Author(s):  
Setareh Habibzadeh ◽  
Hassan Ghasemnejad-Bosra ◽  
Mina Haghdadi ◽  
Soheila Heydari-Parastar
Keyword(s):  
Carboxylic Acid ◽  
Fe3o4 Nanoparticles ◽  
High Efficiency ◽  
Reaction Times ◽  
Chlorosulfonic Acid ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
Solvent Free Conditions

Background: In this study, we developed a convenient methodology for the synthesis of coumarin linked to pyrazolines and pyrano [2,3-h] coumarins linked to 3-(1,5-diphenyl-4,5- dihydro-1H-pyrazol-3-yl)-chromen-2-one derivatives using Chlorosulfonic acid supported Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) catalyst. Materials and Methods:: Fe3O4-PPCA was investigated as an efficient and magnetically recoverable Nanocatalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with a variety of aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be easily recovered by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. Results and Conclusion: The advantages of this protocol are the use of commercially available materials, simple and an inexpensive procedure, easy separation, and an eco-friendly procedure, and it shows good reaction times, good to high yields, inexpensive and practicability procedure, and high efficiency.

Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles

2019 ◽  
Vol 16 (2) ◽  
pp. 258-275 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Reaction Times ◽  
Research Field ◽  
Environmentally Benign ◽  
Metal Catalyst ◽  
Efficient Synthesis ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Harsh Conditions

Background:A wide variety of biological activities are exhibited by N, O and S containing heterocycles and recently, many reports appeared for the synthesis of these heterocycles. The synthesis of heterocycles with the help of metal and non-metal catalyst has become a highly rewarding and important method in organic synthesis. This review article concentrated on the synthesis of S-heterocylces in the presence of metal and non-metal catalyst. The synthesis of five-membered S-heterocycles is described here.Objective:There is a need for the development of rapid, efficient and versatile strategy for the synthesis of heterocyclic rings. Metal, non-metal and organocatalysis involving methods have gained prominence because traditional conditions have disadvantages such as long reaction times, harsh conditions and limited substrate scope.Conclusion:The metal-, non-metal-, and organocatalyst assisted organic synthesis is a highly dynamic research field. For ßthe chemoselective and efficient synthesis of heterocyclic molecules, this protocol has emerged as a powerful route. Various methodologies in the past few years have been pointed out to pursue more sustainable, efficient and environmentally benign procedures and products. Among these processes, the development of new protocols (catalysis), which avoided the use of toxic reagents, are the focus of intense research.

Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

2021 ◽  
Vol 25 ◽  
Author(s):  
Neda Reihani ◽  
Hamzeh Kiyani
Keyword(s):  
Ethylene Glycol ◽  
Ethyl Acetoacetate ◽  
Reaction Medium ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Current Process ◽  
High Yields ◽  
Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

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